Trifluoroacetic acid → HCID 70872913, compound

HRID 1616512Notes

Reaction equation

HRID 1616512 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[CH2:10][NH:11][C:12]([C:14]1[CH:15]=[C:16]([C:30]2[CH:31]=[CH:32][C:33]([N:36]3[CH2:41][CH2:40][CH:39]([NH:42]C(=O)OC(C)(C)C)[CH2:38][CH2:37]3)=[N:34][CH:35]=2)[CH:17]=[C:18]([N:21]([CH2:28][CH3:29])[CH:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[C:19]=1[CH3:20])=[O:13].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:42][CH:39]1[CH2:38][CH2:37][N:36]([C:33]2[N:34]=[CH:35][C:30]([C:16]3[CH:17]=[C:18]([N:21]([CH2:28][CH3:29])[CH:22]4[CH2:23][CH2:24][O:25][CH2:26][CH2:27]4)[C:19]([CH3:20])=[C:14]([CH:15]=3)[C:12]([NH:11][CH2:10][C:3]3[C:4](=[O:9])[NH:5][C:6]([CH3:8])=[CH:7][C:2]=3[CH3:1])=[O:13])=[CH:31][CH:32]=2)[CH2:41][CH2:40]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86672673HCID 86672673, compound

Product 1

HCID 70872913HCID 70872913, compoundYield 903.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl (1-(5-(3-(((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)carbamoyl)-5-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-4-methylphenyl)pyridin-2-yl)piperidin-4-yl)carbamate (0.39 g, 0.058 mmol) in DCM (4 mL) at 0° C., TFA (2 mL) was added and reaction was stirred for 1 h at room temperature. After completion, reaction was concentrated to dryness. The residue was then basified with aqueous sat. bicarbonate solution (30 mL) till pH 8 and aqueous layer extracted with 20% methanol in DCM (50 mL×4). Combined organic phase was dried over Na2SO4 and solvent removed under reduced pressure to afford the title compound (0.3 g, 90.63%) which was used as such for next reaction.

Workup

  1. customreaction
  2. customAfter completion, reaction
  3. concentrationwas concentrated to dryness
  4. extractionextracted with 20% methanol in DCM (50 mL×4)
  5. dry with materialCombined organic phase was dried over Na2SO4 and solvent
  6. customremoved under reduced pressure

Sources & evidence

ORD record
ord-e17bddd996d248b2919ea49a3abcd87f
Source dataset
uspto-grants-2014_07
Patent number
US08765732B2

Reaction notes

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